1218919-30-2Relevant academic research and scientific papers
Preparation of Z-α,β-unsaturated diazoketones from aldehydes. Application in the construction of substituted dihydropyridin-3-ones
Rosset, Isac G.,Burtoloso, Antonio C. B.
, p. 9464 - 9470 (2013)
The stereoselective preparation of α,β-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N-H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the utility of these unsaturated diazoketones for the rapid construction of piperidines.
Z-selective intramolecular horner-wadsworthemmons reaction for the synthesis of macrocyclic lactones
Ando, Kaori,Narumiya, Kenji,Takada, Hirokazu,Teruya, Taiji
scheme or table, p. 1460 - 1463 (2010/06/15)
(Figure Presented) When the substrates (ArO)2P(O)CH 2CO2...CHO (Ar = Ph, o-tBuPh) were added to a THF solution containing 3 equiv of NaH at 0 °C or Nal DBU at rt over 1-10 h, the intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently to give the 12-18-membered-ring lactones in 69-93% yields with 89-100% Z selectivity. On the other hand, (EtO)2P(O)CH2CO2-GHO gave the 13-18-membered-ring lactones in 52-82% yields with 89-99% E selectivity using LiCI-DBU in MeCN or THF.
